2,463

Cudjoe Key, FL Homes

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  • /56

    $579,900

    • 2 Beds
    • 2 Baths
    • 864 Sq Ft

    701 Spanish Main Dr Unit 437, Cudjoe Key, FL 33042

    Introducing an exceptional waterfront investment opportunity in the heart of the Florida Keys! This beautifully remodeled waterfront home in the highly desirable gated community of Venture Out on Cudjoe Key is zoned for minimum one-day vacation rentals, making it an ideal choice for investors or those seeking a turnkey coastal retreat. Step inside and you'll immediately appreciate the home's

    Melissa Graham Bluescape Real Estate

    701 Spanish Main Dr Unit 437, Cudjoe Key, FL 33042
    • /23

      Est $1,366,305 Not Listed For Sale

      21044 7th Ave, Summerland Key, FL 33042

      • 3 Beds
      • 2 Baths
      • 1,400 Sq Ft
      • Built 2001
      21044 7th Ave, Summerland Key, FL 33042

      Last Sold Summary

      • 1% Above List Price
      • $964/SF
      • 78 Days On Market

      Last Sold Price $1,350,000

      Last Listing Agent Diane Corliss Coldwell Banker Schmitt Lower Keys (KW)

  • /64

    $669,000 Open Thu 10:30AM - 1PM

    • 2 Beds
    • 2 Baths
    • 816 Sq Ft

    701 Spanish Main Dr Unit 374, Cudjoe Key, FL 33042

    OCEANFRONT TRANSIENT RENTAL IN VENTURE OUT - CUDJOE KEYAmazing open water views of the sparkling Atlantic set the tone the moment you arrive. From this premier waterfront location, you'll enjoy sweeping vistas of the marina, lagoon, Tiki hut, and the iconic Bird Point sanctuary. Sunrise glows over endless blue water, creating a peaceful and ever-changing coastal backdrop.Positioned on a 35-foot

    Lanny Gardner Bluescape Real Estate

    701 Spanish Main Dr Unit 374, Cudjoe Key, FL 33042
    • /41

      Est $2,286,925 Not Listed For Sale

      20864 4th Ave W, Summerland Key, FL 33042

      • 3 Beds
      • 4 Baths
      • 3,056 Sq Ft
      • Built 2004
      20864 4th Ave W, Summerland Key, FL 33042

      Last Sold Summary

      • 10% Above List Price
      • $679/SF
      • 19 Days On Market

      Last Sold Price $2,075,000

      Last Listing Agent Dave Wiley Coldwell Banker Schmitt Real Estate Co. (KW)

  • /5

    $319,999 Pending

    • 2 Beds
    • 2 Baths
    • 980 Sq Ft

    230 Yardarm Rd, Summerland Key, FL 33042

    This property is above the flood zone so it can be rebuilt, with some restrictions. It does not fall into the Monroe County 50% rule.

    Joe Ordini Keller Williams Key West Compass Realty

    230 Yardarm Rd, Summerland Key, FL 33042
    • /62

      Est $1,699,602 Not Listed For Sale

      1008 Calico Jack Cir, Summerland Key, FL 33042

      • 3 Beds
      • 2 Baths
      • 1,368 Sq Ft
      • Built 1995
      1008 Calico Jack Cir, Summerland Key, FL 33042

      Last Sold Summary

      • 21% Below List Price
      • $1,572/SF
      • 182 Days On Market

      Last Sold Price $2,150,000

      Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  • /41

    $849,000

    • 2 Beds
    • 2 Baths
    • 960 Sq Ft

    154 Cutthroat Dr, Summerland Key, FL 33042

    Beautifully updated 2 bedroom, 2 bathroom home with spacious covered, screened porch overlooking the canal with access to both the Gulf of Mexico and the Atlantic Ocean in just a few minutes. With pride of ownership, this house has been upgraded and well maintained. Many upgrades include: 2024 - New fence with double gates and an entrance gate, gutters, landscaping, tile flooring, freshly painted

    Pamela Stangler Expert Realty LLC

    154 Cutthroat Dr, Summerland Key, FL 33042
    • /35

      Est $1,121,877 Not Listed For Sale

      21024 2nd Ave, Summerland Key, FL 33042

      • 2 Beds
      • 2 Baths
      • 1,313 Sq Ft
      • Built 2005
      21024 2nd Ave, Summerland Key, FL 33042

      Last Sold Summary

      • 9% Above List Price
      • $781/SF
      • 196 Days On Market

      Last Sold Price $1,025,000

      Last Listing Agent The Wesley Group Bascom Grooms Real Estate (KW)

  • /30

    $430,000

    • 1 Bed
    • 1 Bath
    • 748 Sq Ft

    701 Spanish Main Dr Unit 342, Cudjoe Key, FL 33042

    Welcome to your tropical paradise at Venture Out, a gated community on Cudjoe Key, located at Mile Marker 23 in the stunning Florida Keys! This charming, fully furnished 1-bedroom, 1-bath retreat is perfect for enjoying the sun-drenched lifestyle you've been dreaming of. Step into your cozy getaway, featuring a spacious 35' concrete seawall that invites you to explore the waters. Unwind on the

    Lanny Gardner Bluescape Real Estate

    701 Spanish Main Dr Unit 342, Cudjoe Key, FL 33042
    • /31

      Est $529,333 Not Listed For Sale

      22953 John Silver Ln, Summerland Key, FL 33042

      • 2 Beds
      • 2 Baths
      • 960 Sq Ft
      • Built 1983
      22953 John Silver Ln, Summerland Key, FL 33042

      Last Sold Summary

      • 32% Below List Price
      • $810/SF
      • 121 Days On Market

      Last Sold Price $777,500

      Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  • /25

    $569,700

    • 2 Beds
    • 1 Bath
    • 718 Sq Ft

    701 Spanish Main Dr Unit 335, Cudjoe Key, FL 33042

    Licensed nightly rental. Brand new raised Sea Wall!! Discover island living at 701 Spanish Main Dr, Unit 335 in Cudjoe Key, FL. 2Bd/1Ba successful vacation rental located in a premium location on the water with open water views and features a 35' concrete seawall for docking a boat. Dock is equipped with dock posts, cleats, water, and storage. Large patio space to enjoy paradise overlooking the

    Sarah Dolson Keller Williams Key West Compass Realty

    701 Spanish Main Dr Unit 335, Cudjoe Key, FL 33042
    • /40

      Est $887,826 Not Listed For Sale

      20914 7th Ave W, Summerland Key, FL 33042

      • 2 Beds
      • 2 Baths
      • 1,312 Sq Ft
      • Built 1987
      20914 7th Ave W, Summerland Key, FL 33042

      Last Sold Summary

      • 4% Above List Price
      • $648/SF
      • 59 Days On Market

      Last Sold Price $850,000

      Last Listing Agent Diane Corliss Coldwell Banker Schmitt Lower Keys (KW)

  • /46

    $487,000

    • 2 Beds
    • 2 Baths
    • 864 Sq Ft

    701 Spanish Main Dr Unit 659, Cudjoe Key, FL 33042

    Seller is motivated!Coastal Charm Meets Modern Comfort -Welcome to your ideal island escape in the heart of the Lower Keys! This beautifully furnished two-bedroom, two-bath stilt home is located in the welcoming gated residential community of Venture Out on Cudjoe Key--a neighborhood that embraces coastal living and a strong sense of community for all ages.Inside, you'll find a bright and airy

    Lanny Gardner Bluescape Real Estate

    701 Spanish Main Dr Unit 659, Cudjoe Key, FL 33042
    • /47

      Est $1,141,864 Not Listed For Sale

      133 Galleon Ln, Summerland Key, FL 33042

      • 3 Beds
      • 2 Baths
      • 1,780 Sq Ft
      • Built 1994
      133 Galleon Ln, Summerland Key, FL 33042

      Last Sold Summary

      • 2% Above List Price
      • $629/SF
      • 128 Days On Market

      Last Sold Price $1,120,000

      Last Listing Agent Patti Nickless Coldwell Banker Schmitt Real E

  • /29

    $899,000

    • 3 Beds
    • 2 Baths
    • 1,500 Sq Ft

    463 Lesrohde Dr, Ramrod Key, FL 33042

    Don't miss the chance to own this exceptional piece of paradise--schedule a private showing today!Be the first to call this stunning, newly constructed Affinity-built home yours! Located in desirable Ramrod Key, this energy-efficient 3-bedroom, 2-bathroom residence boasts premium quality throughout. Featuring high-end fixtures, Pella impact-resistant windows and doors, and thoughtful

    Sarah Dolson Keller Williams Key West Compass Realty

    463 Lesrohde Dr, Ramrod Key, FL 33042
    • /31

      Est $952,362 Not Listed For Sale

      23038 Sailfish Ln, Summerland Key, FL 33042

      • 2 Beds
      • 2 Baths
      • 1,155 Sq Ft
      • Built 1976
      23038 Sailfish Ln, Summerland Key, FL 33042

      Last Sold Summary

      • 10% Above List Price
      • $749/SF
      • 7 Days On Market

      Last Sold Price $865,000

      Last Listing Agent Miriam Novotny Compass Florida, LLC

  • /52

    $410,000

    • 2 Beds
    • 2 Baths
    • 864 Sq Ft

    701 Spanish Main Dr Unit 635, Cudjoe Key, FL 33042

    Vacation Rental Property with Transient Rentals Allowed! Welcome to the epitome of comfort and convenience in this Palm Harbor fully furnished two-bedroom, two-bath home located within the highly desirable Venture Out Community. This immaculate home is nestled around tropical landscaping with a relaxing patio out back. Step into the open concept living room and well-equipped eat-in kitchen,

    Kim Babenzien Expert Realty LLC (HQ)

    701 Spanish Main Dr Unit 635, Cudjoe Key, FL 33042
    • /42

      Est $1,238,330 Not Listed For Sale

      23028 Sailfish Ln, Summerland Key, FL 33042

      • 3 Beds
      • 2 Baths
      • 1,360 Sq Ft
      • Built 1982
      23028 Sailfish Ln, Summerland Key, FL 33042

      Last Sold Summary

      • 1% Above List Price
      • $919/SF
      • 2 Days On Market

      Last Sold Price $1,250,000

      Last Listing Agent Sandra Tuttle Island Welcome Real Estate

  • /49

    $2,100,000

    • 4 Beds
    • 3 Baths
    • 2,440 Sq Ft

    22542 Jolly Roger Dr, Summerland Key, FL 33042

    This striking 4-bedroom, 3-bathroom home is a testament to coastal architecture, blending rustic design with open, light-filled living spaces that showcase a breathtaking oceanfront setting. Situated on a double lot totaling .32 acres, the property offers an impressive 120 feet of frontage overlooking Cudjoe Bay—creating a rare and commanding presence along the shoreline.Broad covered

    Lauren Dunn Coldwell Banker Schmitt R.E.

    22542 Jolly Roger Dr, Summerland Key, FL 33042
    • /23

      Est $817,921 Not Listed For Sale

      300 Spanish Main Dr, Summerland Key, FL 33042

      • 2 Beds
      • 2 Baths
      • 960 Sq Ft
      • Built 1985
      300 Spanish Main Dr, Summerland Key, FL 33042

      Last Sold Summary

      • 18% Above List Price
      • $721/SF
      • 260 Days On Market

      Last Sold Price $692,500

      Last Listing Agent Diane Corliss Coldwell Banker Schmitt Lower Keys (KW)

  • /16

    $989,999

    • 3 Beds
    • 3 Baths
    • 960 Sq Ft

    22961 John Avery Ln, Summerland Key, FL 33042

    Boater's Paradise in Cudjoe Key under 1 million! Priced to Sell! Bring all offers!Bring your boat, jet skis, and sense of adventure! This upgraded two-story coastal retreat is designed for water lovers, featuring over 60 feet of dock space complete with shore power, plumbing, and brand-new dual jet ski davits plus a boat lift -- perfect for launching into the Florida Keys lifestyle.The lower

    Rayden Vega Casa Miami Real Estate

    22961 John Avery Ln, Summerland Key, FL 33042
    • /40

      Est $857,083 Not Listed For Sale

      22994 Anne Bonny Ln, Summerland Key, FL 33042

      • 3 Beds
      • 2 Baths
      • 1,184 Sq Ft
      • Built 2004
      22994 Anne Bonny Ln, Summerland Key, FL 33042

      Last Sold Summary

      • 2% Above List Price
      • $707/SF
      • 62 Days On Market

      Last Sold Price $837,000

      Last Listing Agent Bascom Grooms Bascom Grooms Real Estate (KW)

  • /6

    $225,000

    • Land

    124 Cutthroat Dr, Cudjoe Key, FL 33042

    Canal front lot in beautiful Cutthroat Harbor Estates. Excellent opportunity to be on the water in a great location. Property currently has concrete columns and slab in place. Possible short sale.

    Jimmy Lane Island Life Realty Experts

    124 Cutthroat Dr, Cudjoe Key, FL 33042
    • /2

      Est $1,572,558 Not Listed For Sale

      1124 de Lussan Ln, Summerland Key, FL 33042

      • 3 Beds
      • 2 Baths
      • 1,404 Sq Ft
      • Built 1989
      1124 de Lussan Ln, Summerland Key, FL 33042

      Last Sold Summary

      • 31% Below List Price
      • $855/SF

      Last Sold Price $1,200,000

      Last Listing Agent Dawn McComish Lokation Real Estate

  • /21

    $575,000

    • 2 Beds
    • 2 Baths
    • 861 Sq Ft

    701 Spanish Main Dr Unit 444, Cudjoe Key, FL 33042

    Affordable piece of paradise! Fully furnished, move in ready, open concept, bright and airy, and freshly painted interior! This 2 bedroom 2 bath home is so spacious you'll be amazed. All new furnishings included! It has a very large kitchen and living area that looks out over the canal, with sliding glass doors out on to the newly painted deck. Minisplits in each room that cool, heat and

    Mary Conklin Action Keys Realty of the Lower FL Keys LLC

    701 Spanish Main Dr Unit 444, Cudjoe Key, FL 33042
    • /2

      Est $876,860 Not Listed For Sale

      1060 Coxon Ln, Summerland Key, FL 33042

      • 2 Beds
      • 2 Baths
      • 1,022 Sq Ft
      • Built 1994
      1060 Coxon Ln, Summerland Key, FL 33042

      Last Sold Summary

      • 5% Below List Price
      • $817/SF

      Last Sold Price $835,000

      Last Listing Agent Wendy Zintsmaster Truman & Co. (KW)

  • /62

    $1,075,000

    • 4 Beds
    • 3 Baths
    • 2,448 Sq Ft

    165 Cutlass Ln, Summerland Key, FL 33042

    Discover your dream waterfront retreat in the Florida Keys. This canal-front home features 4 spacious bedrooms and 3 bathrooms with 2,448 sq. ft. of thoughtfully designed living space, perfect for accommodating family, guests, and entertaining. Enjoy expansive covered balconies on both levels, where you can relax and take in peaceful canal views and the laid-back island lifestyle. The generous

    Justyn Ewald Expert Realty LLC (HQ)

    165 Cutlass Ln, Summerland Key, FL 33042
    • /40

      Est $1,044,259 Not Listed For Sale

      22939 Gasparilla Ln, Summerland Key, FL 33042

      • 3 Beds
      • 2 Baths
      • 1,434 Sq Ft
      • Built 1999
      22939 Gasparilla Ln, Summerland Key, FL 33042

      Last Sold Summary

      • 4% Above List Price
      • $702/SF
      • 159 Days On Market

      Last Sold Price $1,006,436

      Last Listing Agent Diane Corliss Coldwell Banker Schmitt Lower Keys (KW)

  • /27

    $375,000

    • 2 Beds
    • 1 Bath
    • 726 Sq Ft

    701 Spanish Main Dr Unit 536, Cudjoe Key, FL 33042

    Welcome to your slice of the Florida Keys lifestyle! This charming beach-themed retreat is the perfect blend of cozy comfort and coastal style. This 2-bedroom, 1-bathroom turnkey home is move-in ready — whether you're looking for a full-time residence, vacation getaway, or income-producing rental. Step inside to a fresh, inviting living space designed for relaxed island living. The bright white

    Monika Rydzak EXP Realty LLC

    701 Spanish Main Dr Unit 536, Cudjoe Key, FL 33042
    • /15

      Est $3,322,397 Not Listed For Sale

      783 Pattison Dr, Summerland Key, FL 33042

      • 3 Beds
      • 3 Baths
      • 2,578 Sq Ft
      • Built 1980
      783 Pattison Dr, Summerland Key, FL 33042

      Last Sold Summary

      • 16% Above List Price
      • $1,542/SF
      • 290 Days On Market

      Last Sold Price $3,975,000

      Last Listing Agent Lisa Swanson The Agency Florida Keys

  • /11

    $480,000

    • Land

    701 Spanish Main Dr Unit 432, Cudjoe Key, FL 33042

    Discover the ultimate escape! This highly sought-after waterfront RV lot offers everything the coastal enthusiast dreams of, combining luxury amenities with unparalleled nautical access. Located on a wide street this lot is easily accessible for larger RV's and 5th wheels. Features a newer separate concrete parking area for your vehicle and a large level concrete pad for the Rv. Comes complete

    Carmen Brake Waterfront Keys Realty Inc.

    701 Spanish Main Dr Unit 432, Cudjoe Key, FL 33042
    • /2

      Est $1,150,119 Not Listed For Sale

      21056 3rd Ave, Summerland Key, FL 33042

      • 2 Beds
      • 2 Baths
      • 1,726 Sq Ft
      • Built 1978
      21056 3rd Ave, Summerland Key, FL 33042

      Last Sold Summary

      • 15% Below List Price
      • $579/SF

      Last Sold Price $1,000,000

      Last Listing Agent Diane Corliss Coldwell Banker Schmitt Lower Keys (KW)

  • /26

    $229,000 Under Contract

    • 2 Beds
    • 1 Bath
    • 664 Sq Ft

    701 Spanish Main Dr Unit 457, Cudjoe Key, FL 33042

    2 bedroom 1 bath mobile home located at 701 Spanish Main Dr Lot #457 Cudjoe Key FL in Venture Out, an individually owned residential condominium community with 24hr gated security located 20 miles from world famous Key West. This mobile home is on a non-waterfront lot w/ a peek-a-boo view of eastern facing canal. Other ideal use as a ROGO exempt buildable lot for a new elevated home. No age

    Deirdre Praught Florida Keys Realty, Inc.

    701 Spanish Main Dr Unit 457, Cudjoe Key, FL 33042
    • /2

      Est $1,229,472 Not Listed For Sale

      113 Galleon Ln, Summerland Key, FL 33042

      • 3 Beds
      • 3 Baths
      • 2,042 Sq Ft
      • Built 1995
      113 Galleon Ln, Summerland Key, FL 33042

      Last Sold Summary

      • 3% Below List Price
      • $587/SF

      Last Sold Price $1,199,000

      Last Listing Agent Melissa Graham Bluescape Real Estate

  • /40

    $300,000

    • Land

    701 Spanish Main Dr Unit 403, Cudjoe Key, FL 33042

    Transient (1 Day Rental) Rentals Opportunity in the Lower Keys! Buildable RV Lot. Nestled in a serene, well-maintained community, this RV lot offers the ideal spot for your home on wheels, or the opportunity to build your dream home. Boasting a private lot with new landscaping, pea rock and concrete parking pad and is equipped with full hookups including water, sewer, and 30, and 50 amp electric

    Kim Babenzien Expert Realty LLC (HQ)

    701 Spanish Main Dr Unit 403, Cudjoe Key, FL 33042
    • /32

      Est $915,210 Not Listed For Sale

      172 Galleon Ln, Summerland Key, FL 33042

      • 2 Beds
      • 2 Baths
      • 1,232 Sq Ft
      • Built 1980
      172 Galleon Ln, Summerland Key, FL 33042

      Last Sold Summary

      • 11% Above List Price
      • $670/SF
      • 173 Days On Market

      Last Sold Price $825,000

      Last Listing Agent Nira Tocco Coldwell Banker Schmitt RE Co.

    • /33

      Est $1,073,565 Not Listed For Sale

      21012 6th Ave, Summerland Key, FL 33042

      • 2 Beds
      • 2 Baths
      • 1,372 Sq Ft
      • Built 1995
      21012 6th Ave, Summerland Key, FL 33042

      Last Sold Summary

      • 7% Above List Price
      • $729/SF
      • 221 Days On Market

      Last Sold Price $1,000,000

      Last Listing Agent Sandra Tuttle Island Welcome Real Estate

    • /42

      Est $1,321,697 Not Listed For Sale

      20880 6th Ave W, Summerland Key, FL 33042

      • 2 Beds
      • 2 Baths
      • 1,761 Sq Ft
      • Built 1988
      20880 6th Ave W, Summerland Key, FL 33042

      Last Sold Summary

      • 6% Above List Price
      • $710/SF
      • 30 Days On Market

      Last Sold Price $1,250,000

      Last Listing Agent Diane Corliss Coldwell Banker Schmitt Lower Keys (KW)

    • /2

      Est $2,712,586 Not Listed For Sale

      429 Sawyer Dr, Summerland Key, FL 33042

      • 4 Beds
      • 2 Baths
      • 1,999 Sq Ft
      • Built 1974
      429 Sawyer Dr, Summerland Key, FL 33042

      Last Sold Summary

      • 37% Below List Price
      • $988/SF

      Last Sold Price $1,975,000

      Last Listing Agent Jayson Novak Meyer and Boumerhi Realty LLC

    • /2

      Est $856,984 Not Listed For Sale

      22808 Privateer Dr, Summerland Key, FL 33042

      • 3 Beds
      • 2 Baths
      • 1,454 Sq Ft
      • Built 1999
      22808 Privateer Dr, Summerland Key, FL 33042

      Last Sold Summary

      • 6% Below List Price
      • $557/SF

      Last Sold Price $810,000

      Last Listing Agent Diane Corliss Coldwell Banker Schmitt Lower Keys (KW)

Showing Results 281 - 320, Page 8 of 18

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